Water → (1R)-2-[4-(5-Acetyl-2-ethyl-1H-benzimidazol-1-YL)phenyl]-1-methylethyl (4-methylphenyl)sulfonylcarbamate

HRID 50447Notes

Reaction equation

HRID 50447 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:37])[O:13][C@@H:14]([CH3:36])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[C:26]4[CH:27]=[CH:28][C:29]([C:31](=[O:33])[CH3:32])=[CH:30][C:25]=4[N:24]=[C:23]3[CH2:34][CH3:35])=[CH:18][CH:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].O>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12](=[O:37])[O:13][C@H:14]([CH3:36])[CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[C:26]4[CH:27]=[CH:28][C:29]([C:31](=[O:33])[CH3:32])=[CH:30][C:25]=4[N:24]=[C:23]3[CH2:34][CH3:35])=[CH:20][CH:21]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86759400(1S)-2-[4-(5-Acetyl-2-ethyl-1H-benzimidazol-1-YL)phenyl]-1-methylethyl (4-methylphenyl)sulfonylcarbamate

Product 1

HCID 86759399(1R)-2-[4-(5-Acetyl-2-ethyl-1H-benzimidazol-1-YL)phenyl]-1-methylethyl (4-methylphenyl)sulfonylcarbamateYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1R)-1-methyl-2-(4-nitrophenyl)ethyl propanoate (step 1 of Example 248, 1.91 g, 8.05 mmol) in ethanol (20 ml) was added 2N aqueous NaOH (5 ml) at room temperature. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was poured into water, extracted with diethyl ether (2×50 ml). The organic layer was washed with brine, dried (MgSO4), and concentrated. Purification by flash column chromatography eluting with hexane/diethyl ether (1:1) afforded 1.16 g (80%) of title compound as a colorless solid (79% e.e.). Recrystallization from hexane/diethyl ether afforded 717 mg of a colorless needle (99% e.e.).

Workup

  1. extractionextracted with diethyl ether (2×50 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography
  6. washeluting with hexane/diethyl ether (1:1)

Sources & evidence

ORD record
ord-e47c5a794b0f4fcbafd7bb378580decb
Source dataset
uspto-grants-2004_03
Patent number
US06710054B2

Reaction notes

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